【结 构 式】 |
【药物名称】MRS-2179 【化学名称】2'-Deoxy-N6-methyladenosine-3',5'-bisphosphate 【CA登记号】 【 分 子 式 】C11H17N5O9P2 【 分 子 量 】425.23384 |
【开发单位】Natl. Inst. Health, Bethesda, MD (US); Univ. North Carolina, Chapel Hill, NC (US) 【药理作用】PHARMACOLOGICAL TOOLS |
合成路线1
2'-Deoxyadenosine (I) was protected as the diacetate (II) on treatment with acetic anhydride and a catalytic amount of dimethylaminopyridine. Then, reaction with an excess of isopentyl nitrite and diiodomethane under illumination of a tungsten lamp provided iodide (III). Subsequent treatment with ethanolic methylamine effected both deacetylation and substitution of iodide to give 2'-deoxy-N6-methyladenosine (IV). Finally, this was treated with phosphoryl chloride and Proton Sponge(R) in trimethyl phosphate at 0 C, followed by quenching with triethyl ammonium bicarbonate buffer to yield the target bisphosphate.
【1】 Camaioni, E.; et al.; Deoxyadenosine bisphosphate derivatives as potent antagonists at P2Y1 receptors. J Med Chem 1998, 41, 1, 183-190. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 18061 | (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydro-3-furanol | 958-09-8 | C10H13N5O3 | 详情 | 详情 |
(II) | 18062 | [(2R,3S,5R)-3-(acetoxy)-5-(6-amino-9H-purin-9-yl)tetrahydro-2-furanyl]methyl acetate | C14H17N5O5 | 详情 | 详情 | |
(III) | 18063 | [(2R,3S,5R)-3-(acetoxy)-5-(6-iodo-9H-purin-9-yl)tetrahydro-2-furanyl]methyl acetate | C14H15IN4O5 | 详情 | 详情 | |
(IV) | 18064 | N6-Methyl-2'-deoxyadenosine; (2R,3S,5R)-2-(hydroxymethyl)-5-[6-(methylamino)-9H-purin-9-yl]tetrahydro-3-furanol | 2002-35-9 | C11H15N5O3 | 详情 | 详情 |